Caroline D. Ciraolo

Caroline D. Ciraolo, former Acting Assistant Attorney General of the U.S. Department of Justice’s Tax Division, is a partner with Kostelanetz & Fink and a founder of its Washington, D.C. office. Her practice focuses on complex and sophisticated civil tax controversies, including representation in sensitive audits, administrative appeals, and litigation in federal and state courts and tax tribunals, providing related tax advice, including advice on uncertain tax positions, financial reporting, claims for refund, amended returns, voluntary disclosures, and internal investigations, and representing individuals and institutions in criminal tax investigations and prosecutions.

During her tenure with the Department, Caroline was actively involved in all aspects of Tax Division operations and responsible for approximately 500 employees, including more than 360 attorneys in 14 civil, criminal and appellate sections. Under her leadership, the Division reached agreements with 80 Swiss financial institutions that admitted to facilitating tax evasion and the avoidance of reporting requirements by U.S. account holders, and imposed and collected more than $1.36 billion in penalties, increased civil and criminal enforcement with respect to offshore tax evasion, employment tax violations, and traditional tax offenses, assisted the IRS through summons enforcement proceedings, and engaged in affirmative and defensive litigation involving abusive tax shelters and schemes, refund claims, and challenges to statutes and regulations.

Prior to joining the Department, Caroline was Chair of the Tax Controversy and Litigation practice group of a regional firm in Baltimore, Maryland, where she represented individuals and businesses in all phases of state and federal civil tax controversies and criminal tax investigations and prosecutions. She has appeared before the IRS, the Comptroller of Maryland and the D.C. Office of Tax and Revenue, the Maryland Tax Court, the U.S. Tax Court, U.S. District Courts, the Maryland circuit and appellate courts and the U.S. Court of Appeals for the Fourth and Federal Circuits.

Caroline is a Fellow and Regent of the American College of Tax Counsel, a recipient of the ABA Section of Taxation’s Janet Spragens Pro Bono Award, and served as an instructor with the IRS Military Volunteer Income Tax Assistance program at Ft. George G. Meade in Maryland. She has been recognized by Chambers, Benchmark, Best Lawyers in America, Super Lawyers (Top 10 Attorneys in Maryland, and cover story in 2013), EuromoneyLegal Media Group’s Americas Women in Business Law Awards (Best in Tax Dispute Resolution) (2014), and The Daily Record’s Top 100 Women Circle of Excellence. In January, 2017, Caroline was recognized by IRS Chief Counsel William Wilkins with the Chief Counsel Award, the highest honor that can be conferred by that office.

Caroline served as an Attorney Advisor for the Honorable Stanley J. Goldberg of the U.S. Tax Court from 1994 to 1996.

REPRESENTATIVE CIVIL MATTERS

In re Interstate Subpoena for Custodian of Records, Misc. Petition No. 29618M, Circuit Court for Montgomery County, MD (March 27, 2014) (successfully intervened in and obtained a protective order in response to a grand jury subpoena for a client’s records in the possession of an accountant)

United States v. Stahlnecker, Case No. 1:13-cv-01050-MJG, U.S. District Court for the District of Maryland (February 25, 2014) (successfully negotiated a settlement of a suit to reduce a federal tax lien to judgment, resulting in a substantial reduction of assessed trust fund recovery penalties).

Signature Flight Support Corporation v. Supervisor of Assessments for Anne Arundel County, Case No. 13-MI-AA-0579 (1-2), Maryland Tax Court (January 22, 2014) (successfully challenged the denial by the State Department of Assessment and Taxation and the Property Tax Assessment Appeals Board for Anne Arundel County (“PTAAB”) of an application for exemption from property tax on substantial improvements at the Thurgood Marshall Baltimore Washington International Airport, establishing that client was exempt as lessee of property owned by the State and used for a concession at a public airport)

REPRESENTATIVE CRIMINAL MATTERS

Represented individual investigated for filing false income tax returns resulting in a loss of more than $700,000. Negotiated a plea and 2014, persuaded the court to grant a downward variance, resulting in sentence of probation.

Represented individual investigated for filing false income tax returns. Negotiated a misdemeanor plea to a single count of 26 U.S.C. 7207 and successfully argued for a probationary sentence.

Represented individual investigated for failing to file foreign bank account reports and filing false income tax returns resulting in a loss of more than $800,000. Client charged with a single violation of 26 U.S.C. 7201 resulting in an advisory Guideline range of 24 to 30 months. Persuaded court to grant downward variance, resulting in sentence of a year and day, with a recommendation for direct placement to a local residential reentry center (formerly referred to as community confinement or halfway house).

Moderator, "May I Have My Money Back Now Please? The Legal Landscape Overseas And Strategies To Navigate International Asset Seizures", 10th Annual Tax Controversy Forum, New York University, New York, NY (June 22, 2018)

Speaker, "AML And Tax – What Every AML Officer Should Know About The New And Emerging Tax Issues", 2017 American Bankers Association and the American Bar Association Financial Crimes Enforcement Conference, National Harbor, MD (December 4, 2017)